Sodium Carbonate → HCID 59380190, compound

HRID 2353751Notes

Reaction equation

HRID 2353751 reaction equation
Cl[C:2]1[N:7]=[C:6]([C:8]([S:11]([CH:14]2[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]2)(=[O:13])=[O:12])([CH3:10])[CH3:9])[CH:5]=[C:4]([N:20]2[CH2:25][CH2:24][O:23][CH2:22][C@@H:21]2[CH3:26])[N:3]=1.C(=O)([O-])[O-].[Na+].[Na+].CC1(C)C(C)(C)OB([C:41]2[CH:47]=[CH:46][C:44]([NH2:45])=[CH:43][CH:42]=2)O1>CN(C=O)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.O.C(OCC)(=O)C.COCCOC.C(O)C>[CH:14]1([S:11]([C:8]([C:6]2[CH:5]=[C:4]([N:20]3[CH2:25][CH2:24][O:23][CH2:22][C@@H:21]3[CH3:26])[N:3]=[C:2]([C:41]3[CH:47]=[CH:46][C:44]([NH2:45])=[CH:43][CH:42]=3)[N:7]=2)([CH3:10])[CH3:9])(=[O:13])=[O:12])[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1

Participants

10

Reactant 3

HCID 10340Sodium CarbonateHCID 27346204-(Tetramethyl-1,3,2-dioxaborolan-2-yl)anilineHCID 59379899HCID 59379899, compound

Product 1

HCID 59380190HCID 59380190, compoundYield 83.8%

Reagents, catalysts & solvents 6

HCID 178418476HCID 178418476, compoundCatalystHCID 702EthanolSolventHCID 962WaterSolvent2×HCID 6228DimethylformamideSolventHCID 80711,2-DimethoxyethaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 2-chloro-4-(2-cyclohexylsulfonylpropan-2-yl)-6-[(3S)-3-methylmorpholin-4-yl]pyrimidine (1.18 g, 2.94 mmol), 2M aqueous sodium carbonate solution (5.5 mL, 11.00 mmol) and 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (0.907 g, 4.14 mmol) in a mixture of DMF (5 mL), water (12.50 mL), ethanol (5.00 mL) and DME (5.00 mL) was purged with nitrogen for 10 minutes before being treated with bis(triphenylphosphine)palladium(II) chloride (0.111 g, 0.16 mmol). The stirred mixture was heated to 80° C. and stirred under nitrogen for 2.5 hours. The reaction mixture was cooled and treated with ethyl acetate (50 mL) and water (50 mL). The organic layer was separated and the aqueous re-extracted with ethyl acetate (2×30 mL). The combined organics were washed with brine, dried (MgSO4) and evaporated to afford the crude product, which was purified by flash silica chromatography, elution gradient 25 to 75% ethyl acetate in isohexane, to give the desired material (1.130 g).

Workup

  1. customwas purged with nitrogen for 10 minutes
  2. temperatureThe reaction mixture was cooled
  3. customThe organic layer was separated
  4. extractionthe aqueous re-extracted with ethyl acetate (2×30 mL)
  5. washThe combined organics were washed with brine
  6. dry with materialdried (MgSO4)
  7. customevaporated
  8. customto afford the crude product, which
  9. customwas purified by flash silica chromatography, elution gradient 25 to 75% ethyl acetate in isohexane

Sources & evidence

ORD record
ord-1bbdcd09b7ac4520b7c7a7e1afe5ac4d
Source dataset
uspto-grants-2010_07
Patent number
US07750003B2

Reaction notes

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